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Sur la structure des terpénylphénols obtenus en condensant le camphène avec le phénol, et celle de leurs dérivés hydrogénés à odeur boisée
Author(s) -
Demole Edouard
Publication year - 1964
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19640470142
Subject(s) - chemistry , phenols , cyclohexanol , camphene , sandalwood , phenol , organic chemistry , medicinal chemistry , condensation , catalysis , stereochemistry , essential oil , chromatography , physics , thermodynamics , archaeology , history
Abstract The mixture obtained from the well‐known BF 3 ‐catalyzed condensation of camphene and phenol contains at least nine terpeno‐phenols. The major components are o‐ ( p ‐) (2,2, exo‐3‐trimethyl‐exo‐5‐norbornyl)‐phenols, accompanied by some o‐ ( p ‐) (exo‐2‐borny1)‐phenols and smaller amounts of o‐ ( p ‐) (1,3,3‐trimethyl‐exo‐6‐norborny1)‐ phenols. Further, very small amounts (>1%) of the three corresponding meta ‐substituted phenols also occur in the condensation mixture. On catalytic hydrogenation, these m ‐isomers lead to 3‐terpenyl‐cyclohexanols characterized by a powerful odour of sandalwood. Most surprisingly, the 2‐ and 4‐terpenyl‐cyclo‐hexanols obtained in the same way from the o‐ and p ‐terpenyl‐phenols are almost odourless. The sandalwood odour appears, therefore, to be highly characteristic of the 3‐substituted cyclohexanols, and this fact has been conclusively verified by the unambiguous synthesis of the axial and equatorial epimers of 3‐(2,2, exo‐3‐trimethyl‐exo‐5‐norbornyl)‐cyclohexanol.